diff --git a/vscode/src/client.ts b/vscode/src/client.ts
index b687be4ed..a5598a960 100644
--- a/vscode/src/client.ts
+++ b/vscode/src/client.ts
@@ -148,17 +148,27 @@ function collectClientOptions(
     });
   }
 
-  // Because of how default gems are installed, the entry in the `GEM_PATH` is actually not exactly where the files
-  // are located. With the regex, we are correcting the default gem path from this (where the files are not located)
-  // /opt/rubies/3.3.1/lib/ruby/gems/3.3.0
-  //
-  // to this (where the files are actually stored)
-  // /opt/rubies/3.3.1/lib/ruby/3.3.0
   ruby.gemPath.forEach((gemPath) => {
     documentSelector.push({
       language: "ruby",
-      pattern: `${gemPath.replace(/lib\/ruby\/gems\/(?=\d)/, "lib/ruby/")}/**/*`,
+      pattern: `${gemPath}/**/*`,
     });
+
+    // Because of how default gems are installed, the gemPath location is actually not exactly where the files are
+    // located. With the regex, we are correcting the default gem path from this (where the files are not located)
+    // /opt/rubies/3.3.1/lib/ruby/gems/3.3.0
+    //
+    // to this (where the files are actually stored)
+    // /opt/rubies/3.3.1/lib/ruby/3.3.0
+    //
+    // Notice that we still need to add the regular path to the selector because some version managers will install gems
+    // under the non-corrected path
+    if (/lib\/ruby\/gems\/(?=\d)/.test(gemPath)) {
+      documentSelector.push({
+        language: "ruby",
+        pattern: `${gemPath.replace(/lib\/ruby\/gems\/(?=\d)/, "lib/ruby/")}/**/*`,
+      });
+    }
   });
 
   // This is a temporary solution as an escape hatch for users who cannot upgrade the `ruby-lsp` gem to a version that
diff --git a/vscode/src/test/suite/client.test.ts b/vscode/src/test/suite/client.test.ts
index cc516ede6..687c243dd 100644
--- a/vscode/src/test/suite/client.test.ts
+++ b/vscode/src/test/suite/client.test.ts
@@ -674,6 +674,7 @@ suite("Client", () => {
       workspaceRubyFilter,
       workspaceERBFilter,
       bundledGemsFilter,
+      defaultPathFilter,
       defaultGemsFilter,
     ] = client.clientOptions.documentSelector!;
 
@@ -702,6 +703,11 @@ suite("Client", () => {
       new RegExp(`ruby\\/\\d\\.\\d\\.\\d\\/\\*\\*\\/\\*`),
     );
 
+    assert.match(
+      (defaultPathFilter as TextDocumentFilter).pattern!,
+      /lib\/ruby\/gems\/\d\.\d\.\d\/\*\*\/\*/,
+    );
+
     assert.match(
       (defaultGemsFilter as TextDocumentFilter).pattern!,
       /lib\/ruby\/\d\.\d\.\d\/\*\*\/\*/,